He was born in County Armagh in Ireland and in 1832 came to Canada with his family and his father established a farm in Etobicoke. Smith went into commerce, first working as a clerk in several Toronto stores, and then opening is own wholesalers in London, Ontario in 1849. After a few years of limited business, the arrival of the railway in London set off an economic boom and Smith prospered greatly. He expanded his business interests, including becoming the primary shareholder in the Toronto Street Railways.

The Senator's residence in Toronto, seen in the 1890s.

Smith made his fortune with the streetcar service generating record products by cutting costs, not replacing aged cars and requiring his employees to work 14 hour days, six days a week for $8 to $9 a week. When his workers threatened to join the Knights of Labor trade union he locked them out resulting in three days of violent protests. Mayor William Holmes Howland and the press supported the workers' right to organize but Smith refused to allow a union and criticized the city government for failing to maintain order. In the end, Smith allowed limited pay increases but refused to allow a union and fired the organizers prompting a strike and the establishment of a rival, worker run "Free Bus Company" which was soon out of business when its fleet was destroyed by fire. Smith's actions alienated the Toronto working class, particularly Catholic workers among whom he hoped to build a political base. Smith sold his share of the TSR to the city in 1881 for $500,000.[1]

In politics, Smith was an advocate of the rights of Irish Catholics and lobbied for the appointment of Irish Catholics to patronage positions. In 1872, he lobbied Macdonald for the gradual release of Fenian raiders who had attempted military attacks on Canadian soil in order to promote Irish independence.